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Coming Ashore: Rum Runners Of The East End

Originally Posted: July 23, 2008

Ben Amato

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U.S. Coast Guard Revenue Cutter Seneca in 1914. Photo by Outlanderssc

East Hampton - Floating 12 miles off the coast of Long Island lies the vanished kingdom of Rum Row. For over a dozen years schooners, steamers, and converted fishing trawlers sold Canadian whiskey and Bahamian rum to thirsty Americans during the Prohibition years. From the harbors at Greenport and Montauk, to the small bays of the South Shore, rum runners in small boats would head to sea to load hundreds of cases of contraband and then evade, outrun, or bribe their way past Coast Guard and local police patrols.

New York speakeasies of the Roaring 1920s poured this illegal "hooch." The Gold Coast of Nassau County sipped their illicit champagne and the East End of Long Island flourished as a conduit for the rum runners. It also served as a criminal nursery for young hoodlums, eager to make a buck and a name. Nineteen-year-old Al Capone learned his murderous trade rum running in Amityville. Dutch Schultz became the Island's kingpin, bullying, bribing, or beating his way to controlling the entire flow, from the boats to the beach to the bar.

Rum runner sloop "Kirk and Sweeney" with contraband stacked on deck in 1924.
Photo U.S. Coast Guard

Long Island high life flourished, fueled by booze, big money and the famous that were drawn to East End. The Canoe Place Inn (C.P.I.) of Hamptons Bays was known as the summer headquarters of Tammany Hall, with New York's corrupt politicians enjoying the flow of illegal alcohol and wealth. Even Presidential candidate and then New York Governor Al Smith frequented the old C.P.I. Merrick Road became "Glitter Alley," featuring entertainment legends Rudy Valle, Eddie Cantor, and Sophie Tucker. Sunrise Highway turned into "The Great Light Way" and Motor Parkway, originally built by the Vanderbilt's as a private racecourse, was nicknamed Rumrunner's Road with nightly competition between bootleggers and the police.

Captain William McCoy is credited for establishing Rum Row, the line of boats that would anchor off the South Shore of Long Island. He would fill the holds of his schooner 'Arethusa' with Johnny Walker Red and Bacardi from two small French owned islands off the coast of Newfoundland. While other rum runners would water down their goods, McCoy had a reputation for fair dealing and quality products. He was "The Real McCoy."

Captain William McCoy

The late ex-Congressman Perry Duryea remembered Prohibition from his Montauk childhood. In a recorded oral history compiled by the East Hampton Library he reminisced how "...there was one basic industry in Montauk specifically...that was the product of the rum running days. And I remember when I was in the local school and I would look out over the Atlantic Ocean and see the boats anchored off there that had run down from Saint-Pierre and Miquelon, with their quantity of refreshments. They would anchor outside of the legal limit and then the fishermen would go out in the evening and come [back] in the morning rather than leaving in the morning and returning in the evening...and it really was an industry here too. Most any able-bodied man would have the news when a boat happened to be coming in and they would help with the unloading process."

Not all the booze made it into Manhattan and soon the glamorous and famous were draw to the East End by the wealth and watering holes of Montauk, the Hamptons, Greenport, and the North Fork. Southampton's Red Bar Brasserie began as a speakeasy and East Hampton's Hedges Inn still has a hideaway used to store the "hooch." East Quogue had a club called Jameson's offering entertainment and refreshments.

Al Capone

Montauk had a fleet of ferries and "party boats" that would take passengers from the Long Island Rail Road to Boston, detouring beyond the U.S. territorial line for a voyage of booze and gambling. The most glamorous speakeasy on the East End was the Island Club, located on Star Island on the grounds of the Montauk Yacht Club. Carl Fisher built this playground for the rich and thirsty and it brought out such celebrities as John Barrymore, Errol Flynn, Ernest Hemmingway, and even the then mayor of New York, Jimmy Walker. This nightclub and casino operated openly until a raid by the Feds in 1930.

Greenport has Claudio's, America's oldest family restaurant, established in 1870 by its founder Manuel Claudio. During Prohibition, under the management of Frank Claudio, the downstairs became a fine French restaurant while upstairs the party continued non-stop for over a dozen years. The illegal spirits would come in by the boatload, floated under the building and hoisted through a trapdoor, which still exists behind the bar. This National Historic Registered Building is a piece of living history and at it's heart is a huge Indian Mahogany bar, lined with Carrara marble, brought in from New York City in 1886. Patrons today can enjoy the fine service of over 100 employees and view Claudio's fabled past via old photographs and memorabilia that line the walls. The family still operates the legendary restaurant and Bill Jr., Janice, Kathy, Betsy and Jerry are there to ensure all eat, drink and be merry just as all their patrons have for over 138 years. The History Channel and Channel 12 News just completed television programs centering on Claudio's bootlegging legacy but to enjoy this piece of Long Island's past, a visit is required.

Bill Claudio, Jr., the present owner of Claudio's, and the
infamous trap door.

Mattituck featured two speakeasies of note, the Anchor Inn, which burned down during the 1950s and the Old Mill Inn, which still operates and serves fine food, and now legal spirits. Managed by Barbara Pepe and Bia Lowe, this restaurant sits on the Mattituck Creek, a mile inland from the Inlet. The trapdoor to their Prohibition past sits in their kitchen, under the main stove but their bar area, main dining salon and outdoor, dockside deck all invoke their celebrated history. Rumor has it that Clark Gable and Carol Lombard would vacation there, together, away from the prying eyes of New York newspapers.

From the rafters in their bar area to the supports that hold up the building, Long Island's past is both seen and felt at the Old Mill Inn. Patrons would "brand" their names in the wood, with some signatures dating back to the 1830s, when the building was a grinding mill which used the creek's tidal power to produce flour. The actual stone wheel is located beside the parking lot and the mill's spindle still runs through the bar area. Photographs and old posters fill the walls and the historic ambiance is enhanced even more when one of the co-owners (a famous newswoman from CNN and Fox) docks her 80 foot 1947 Trumpy, alongside the dining area. This a sister ship of the 1925 Presidential Yacht the U.S.S. Sequoia.

Barbara and Bia have blended the history of the Old Mill Inn with the most current trends. There's a rum runner drink served at the bar, special dinners put together by the Slow Food Organization, and even mid-week dinner cruises aboard the Captain Bob V. This hour long after-dinner cruise follows the course of the old rum runners, who would supply the speakeasies with their illicit stock.

The "Nobel Experiment" of Prohibition left a mark on our Island because of the unique bays, inlets and harbors that made the East End a perfect point of entry for the illicit trade. This waterside chapter of our history can be seen, tasted and enjoyed even today when you visit the remnants of our bootlegging past. Besides, it is always more fun to discover our history by visiting the "Real McCoys," the actual places where you can get a taste and the buzz of our rum running past.

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Guest (Lon S. Cohen) from Southampton, NY says::
Great article. I happened to catch the Rumrunners TV documentary and then reading this article really brought it "home" literally. Thanks for the history of the East End's pirate past. Who knew that it was illegal hooch that really made the East End the playground of the rich and famous that it is today. LOL. We've come a long way, or, have we??? Looking forward to more of your articles Ben.
Aug 6, 2008 12:00 am


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